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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Taylor Adkins# | 16 | 2069-2080 | |
| 2 | Athena Aria* | 15 | 2045-2058 | |
| 2 | Ed Barker* | 15 | 2027-2039 | |
| 4 | Regnaleb Sivart | 14 | 2032-2045 | |
| 5 | Always A. Bummus | 13 | 2066-2078 | |
| 5 | John Marston* | 13 | 2052-2064 | |
| 5 | Anthony Parco | 13 | 2052-2061 | |
| 5 | Phillip Thompson* | 13 | 2018-2028 | |
| 5 | PDub Woods | 13 | 2065-2078 | |
| 10 | Kevin Choate* | 12 | 2032-2044 | |
| 10 | Joey Moose Jr. | 12 | 2066-2077 | |
| 10 | Joey Slothface | 12 | 2028-2041 | |
| 13 | John Cowgill# | 11 | 2068-2080 | |
| 13 | Glyn Davies* | 11 | 2044-2057 | |
| 13 | Acheoar Hippocrites* | 11 | 2053-2067 | |
| 13 | Allegra McArena* | 11 | 2052-2067 | |
| 13 | Esteban Rodriguez* | 11 | 2017-2029 | |
| 13 | Ryan Rose* | 11 | 2031-2042 | |
| 13 | Guy Roussy | 11 | 2067-2079 | |
| 13 | Starscream* | 11 | 2053-2064 | |
| 13 | Greg Steiner* | 11 | 2018-2031 | |
| 13 | Oerjan Thrastarsen* | 11 | 2055-2067 | |
| 13 | Guy Walker* | 11 | 2021-2034 | |
| 24 | Evil Dictator | 10 | 2047-2059 | |
| 24 | Wutcanisae Eksepurwelkam* | 10 | 2054-2065 | |
| 24 | Rayz Funk | 10 | 2035-2047 | |
| 24 | Booze Gooser* | 10 | 2045-2054 | |
| 24 | Billy Grier | 10 | 2038-2049 | |
| 24 | Doc Holliday# | 10 | 2072-2080 | |
| 24 | Straightgas Homie* | 10 | 2042-2055 | |
| 24 | Wright Indadert* | 10 | 2051-2062 | |
| 24 | Khamati Kahn | 10 | 2018-2029 | |
| 24 | Penny Kowers* | 10 | 2017-2034 | |
| 24 | Blu Line* | 10 | 2027-2040 | |
| 24 | Gionna Morgan* | 10 | 2048-2060 | |
| 36 | Virzeiros Balqen | 9 | 2030-2045 | |
| 36 | Andy Beans | 9 | 2065-2080 | |
| 36 | Walker Cato | 9 | 2034-2047 | |
| 36 | Xavier Crawford | 9 | 2053-2066 | |
| 36 | Peter Dawson | 9 | 2026-2036 | |
| 36 | Colben Fairborn | 9 | 2026-2038 | |
| 36 | Kelvin Gauzeman | 9 | 2058-2070 | |
| 36 | Ransom Jones* | 9 | 2066-2076 | |
| 36 | Ryan Lee | 9 | 2067-2080 | |
| 36 | Brent Lomew* | 9 | 2029-2041 | |
| 36 | Parker Parton | 9 | 2045-2058 | |
| 36 | Jormungandr Ragnarok | 9 | 2046-2056 | |
| 36 | Romeo Rosas* | 9 | 2056-2070 | |
| 36 | Ike Sampson | 9 | 2055-2067 | |
| 36 | Sportsboy57 | 9 | 2045-2059 | |
| 36 | Matt Stro | 9 | 2053-2065 | |
| 36 | Harry Styles* | 9 | 2028-2039 | |
| 36 | Shoto Todoroki* | 9 | 2044-2056 | |
| 36 | Toby Ziegler | 9 | 2065-2071 | |
| 55 | Cesar Azuaje | 8 | 2050-2062 | |
| 55 | Calm Chicken | 8 | 2067-2080 | |
| 55 | Roquefort Cotswald | 8 | 2065-2077 | |
| 55 | Professor Croakwell# | 8 | 2071-2080 | |
| 55 | Psy Duck* | 8 | 2054-2066 | |
| 55 | Amp Dupree | 8 | 2029-2041 | |
| 55 | Damian Jansen-Crenshaw | 8 | 2045-2056 | |
| 55 | Chaz LaLocke | 8 | 2017-2030 | |
| 55 | Hayley MaConnell* | 8 | 2026-2037 | |
| 55 | Man O'Rite | 8 | 2052-2067 | |
| 55 | Usada Pekora* | 8 | 2061-2074 | |
| 55 | Holly Sheet# | 8 | 2067-2080 | |
| 55 | Samuel Smoltz# | 8 | 2073-2080 | |
| 55 | Danny Sullivan | 8 | 2041-2051 | |
| 55 | Johnny Tatum | 8 | 2065-2078 | |
| 55 | Wayne Wheeler | 8 | 2057-2066 | |
| 71 | Sam Antonio | 7 | 2048-2062 | |
| 71 | Matthew Auston | 7 | 2019-2031 | |
| 71 | Calvin Ball | 7 | 2064-2074 | |
| 71 | Frederick Birdington | 7 | 2025-2037 | |
| 71 | D'Aroldis Borkman* | 7 | 2018-2031 | |
| 71 | Siegmeyer of Catarina | 7 | 2065-2077 | |
| 71 | Michael Dion | 7 | 2039-2049 | |
| 71 | Brigham Irons | 7 | 2064-2075 | |
| 71 | Ultimo Kahn# | 7 | 2072-2080 | |
| 71 | Ryan Knock | 7 | 2057-2065 | |
| 71 | Colby Koffman | 7 | 2066-2077 | |
| 71 | Aiden MacDougall | 7 | 2036-2050 | |
| 71 | Dude Manbro | 7 | 2031-2039 | |
| 71 | Romeo McFlourish | 7 | 2067-2080 | |
| 71 | Glenallen Mixon* | 7 | 2043-2055 | |
| 71 | Barack Obama* | 7 | 2030-2040 | |
| 71 | Yakul Red | 7 | 2045-2056 | |
| 71 | Beauregard Rove | 7 | 2055-2067 | |
| 71 | Poe Scott* | 7 | 2045-2060 | |
| 71 | Victoria Secret* | 7 | 2017-2028 | |
| 71 | Aduke Singh* | 7 | 2043-2054 | |
| 71 | Stryker Spinrate | 7 | 2031-2042 | |
| 71 | Dizzy Stoner | 7 | 2061-2072 | |
| 71 | Ryan Stryker Jr.* | 7 | 2055-2069 | |
| 71 | Lizzie WOOOOHOOOO# | 7 | 2073-2080 | |
| 96 | Pax Abadeer* | 6 | 2042-2055 | |
| 96 | Alexander Benjamin | 6 | 2047-2062 | |
| 96 | Erick Bolanos | 6 | 2039-2049 | |
| 96 | Bubbles | 6 | 2060-2068 | |
| 96 | Chris P. Cream | 6 | 2058-2068 |
